Pyridine → 5-[4-(4-tert-Butyl-phenoxy)-phenylsulfamoyl]-2-methyl-benzoic acid

HRID 855986

Reaction equation

HRID 855986 reaction equation
[C:1]([C:5]1[CH:18]=[CH:17][C:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl[S:20]([C:23]1[CH:24]=[CH:25][C:26]([CH3:32])=[C:27]([CH:31]=1)[C:28]([OH:30])=[O:29])(=[O:22])=[O:21].N1C=CC=CC=1>O1CCCC1.C(OCC)(=O)C>[C:1]([C:5]1[CH:18]=[CH:17][C:8]([O:9][C:10]2[CH:11]=[CH:12][C:13]([NH:16][S:20]([C:23]3[CH:24]=[CH:25][C:26]([CH3:32])=[C:27]([CH:31]=3)[C:28]([OH:30])=[O:29])(=[O:22])=[O:21])=[CH:14][CH:15]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 1049PyridineHCID 824984-(4-Tert-butylphenoxy)anilineHCID 3084495-(Chlorosulfonyl)-2-methylbenzoic acid

Product 1

HCID 589370405-[4-(4-tert-Butyl-phenoxy)-phenylsulfamoyl]-2-methyl-benzoic acidYield 82%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(4-tert-butyl-phenoxy)-phenylamine (0.1 g, 0.41 mmol). 5-chlorosulfonyl-2-methylbenzoic acid (0.097 g, 0.41 mmol) and pyridine (0.1 ml, 1.24 mmol) in 2 ml anhydrous tetrahydrofuran was heated at 60° C. for 2 hr. The reaction mixture was cooled to room temperature and diluted with 30 ml ethyl acetate. The ethyl acetate solution was washed sequentially with 25 ml 1N aqueous hydrochloric acid solution and 25 ml brine, dried (anhydrous sodium sulfate) and concentrated to dryness under reduced pressure. The crude product was purified by preparative thick layer chromatography (silica gel), eluting with 9:1 chloroform/methanol to yield the title compound.

Workup

  1. washThe ethyl acetate solution was washed sequentially with 25 ml 1N aqueous hydrochloric acid solution and 25 ml brine
  2. dry with materialdried (anhydrous sodium sulfate)
  3. concentrationconcentrated to dryness under reduced pressure
  4. customThe crude product was purified by preparative thick layer chromatography (silica gel)
  5. washeluting with 9:1 chloroform/methanol

Sources & evidence

ORD record
ord-d16715c87bba49a5856bec6decc7aad8
Source dataset
uspto-grants-2007_08
Patent number
US07262318B2

Linked notes

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